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The longest cocktail name on Hank’s Oyster Bar‘s menu takes up two lines and contains 18 words: “An Italian Gentleman Riding His Bike Through the Piazza with His Pant Leg Rolled Slightly Above His Ankle.”

The gin-Aperol-grapefruit-mint mix doesn’t even hold the record for breathless cocktail names. For one week last spring, the Hill location of the oyster bar devoted an entire menu to the “Story of the Italian Gentleman” with one drink name that stretched 28 words over three lines: 

So what’s the deal with the Italian Gentleman? Where did this elaborate inside joke come from?

Michael Saccone, the bar manager and assistant general manager at Hank’s on the Hill, says one day about two years ago, he and a former general manager were trying to name a drink with Aperol. The bitter orange Italian aperitif inspired the name “an Italian Gentleman.” And then things snowballed. They kept adding on to it, making it longer and longer. The pant leg bit was inspired by Saccone, who rolls his pant legs up when he bartends, because he doesn’t like “things on my ankles.”

Hank’s Oyster Bar had fun names before, but Saccone says this was the one that opened the flood gates to even more obscure and zany monikers. Just look at some of the other current cocktails: “Who Does Number 2 Work For?” and “Jason is Not Here Tonight.”

“I kind of like to make people a little uncomfortable when they order drinks,” Saccone says. “I just think it’s funny to watch them look at the menu and not have any idea what they want just because the names are so ridiculous and have nothing to do with the actual drinks themselves.”

Plus, it’s also a bit of self-mockery meant to poke fun at bartender pretentiousness. “We try to do very serious drinks in the least serious way possible,” Saccone says.

The Italian Gentleman remains a permanent fixture on Hank’s menu. The man now has an entire history and personality. He has a yacht named “Impulse.” He enjoys charcuterie. He argues with American con men.

“In my head, he is Jude Law from The Talented Mr. Ripley,” Saccone says.

But at what point does the story get too long-winded? How long is too long for a cocktail name?

“Two sentences might be pushing it,” Saccone says. “One sentence is good.”

Does that mean he would never do a three-sentence cocktail name?

“I wouldn’t say never for anything that we do here. We’ll do it just because people say we can’t do it. If you don’t think we can do it, we will do it.”

And if I don’t think they can do it…

“I might have to take two or three cocktails off to get it to fit, but we’ll get it on there.”

Top photo by Jessica Sidman. Bottom photo courtesy Hank’s Oyster Bar.